Abstract
Isostearic acids (IA) are highly utilized for industrial purposes especially in the area of biolubricants, such as cosmetics and slip additives for polyolefin and related copolymer films. This study was designed to develop a zeolitic catalysis process for efficient IA production through isomerization of fatty acids. The process utilized zeolite protonated Ferrierite with a small amount of base additive to neutralize (i.e., poison) the acidic sites on the external surfaces of the zeolite particles to prevent side reactions. Of the six base additives examined, the proton sponge combined with the zeolite protonated Ferrierite was found to be the most effective for this isomerization. With only 0.5 wt% proton sponge additive to 5.0 wt% Ferrierite, the dimers were successfully suppressed from 20.6 wt% yield to 2.42 wt% with an IA yield of 83.4 wt% and a 98 % conversion.
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References
Kunkeler PJ, Downing RS, van Bekkum H (2001) The use of bulky molecules as probes for investigating the contributions of the external and internal pore-wall activities of zeolite catalysts. In: van Bekkum H, Flanigen EM, Jacobs PA, Jansen JC (eds) Introduction to zeolite science and practice—2nd completely revised and expanded edition. Elsevier, Amsterdam, pp 987–1001
Ginter DM, Went GT, Bell AT, Radke CJ (1992) A physicochemical study of the aging of colloidal silica gels used in zeolite Y synthesis. Zeolites 12:733–741
Rachwalik R, Olejniczak Z, Jiao J, Huang J, Hunger M, Sulikowski B (2007) Isomerization of α-pinene over dealuminated ferrierite-type zeolites. J Catal 252:161–170
Creyghton EJ, Elings JA, Downing RS, Sheldon RA, van Bekkum H (1996) New multifunctional probe for testing outer surface activity of zeolites: application to surface-located platinum clusters and acid sites. Microporous Mater 5:299–307
Chen CS, Heights B, Tabak SA (1986) Production of lubricant range hydrocarbons from light olefins. US Patent 4,568,786
Chen CS, Heights B (1987) Production of lubricant range hydrocarbons from light olefins. US Patent 4,658,079
Blain DA, Page NM, Young LB (1991) Olefin oligomerization with surface modified zeolite catalyst. US Patent 5,026,933
Ngo HL, Hoh E, Foglia TA (2012) Improved synthesis and characterization of saturated branched-chain fatty acid isomers. Eur J Lipid Sci Technol 114:213–221
Ngo HL, Foglia TA (2014) Process for preparing saturated branched chain fatty acids. US Patent 8,748,641 B2
Ngo HL (2014) Improved zeolite regeneration processes for preparing saturated branched-chain fatty acids. Eur J Lipid Sci Technol 116:645–652
Ngo HL, Ashby RD, Nuñez A (2012) Selective microbial degradation of saturated methyl branched-chain fatty acid isomers. J Am Oil Chem Soc 89:1885–1893
Zhang S, Zhang Z, Steichen D (2005) Skeletal isomerization of alkyl esters and derivatives prepared therefrom. US Patent 6,946,567
Tomifuji T, Abe H, Matsumura Y, Sakuma Y (1997) Process for the preparation of branched chain fatty acids and alkyl esters thereof. US Patent 5,677,473
Wiedemann SCC, Stewart JA, Soulimani F, Bergen-Brenkman T, Langelaar S, Wels B, Peinder P, Bruijnincx PCA, Weckhuysen BM (2014) Skeletal isomerization of oleic acid over ferrierite in the presence and absence of triphenylphosphine: pore mouth catalysis and related deactivation mechanisms. J Catal 316:24–35
Allman T, Goel RG (1982) The basicity of phosphines. Can J Chem 60:716–722
Lawrence SA (2004) Amines, synthesis, properties, and applications. Cambridge University Press, Cambridge, pp 73–74
Gero A, Markham JJ (1951) Studies of pyridines: I. the basicity of pyridine bases. J Org Chem 16:1835–1838
Van Bekkum H, Flanigen EM, Jacobs PA, Jansen JC (eds) (2001) Introduction to zeolite science and practice. Elsevier, Amsterdam, pp 369–418
Brown HC, Kanner B (1966) Preparation and reactions of 2,6-di-t-butylpyridine and related hindered bases. A case of steric hindrance toward the proton. J Am Chem Soc 88(5):986–992
Rodriguez I, Sastre G, Corma A, Iborra S (1999) Catalytic activity of proton sponge: application to Knoevenagel condensation reactions. J Catal 183(1):14–23
Zhao X, Bu X, Wu T, Zheng ST, Wang L, Feng P (2013) Selective anion exchange with nanogated isoreticular positive metal-organic frameworks. Nat Commun 4:2344
Acknowledgments
I thank Mr. Bun Hong-Lai and Mrs. Renee Latona for experimental assistance, Dr. Michael Haas for his critical reading of the manuscript, and Mr. Zekai Lin from the University of Chicago for determining the dimensions of the base additives. Finally, I would like to thank NIFA-AFRI (Grant award # 2013-67021-21142) for providing partial funding support.
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Ngo, H.L. Lewis Base Additives Improve the Zeolite Ferrierite-Catalyzed Synthesis of Isostearic Acids. J Am Oil Chem Soc 92, 613–619 (2015). https://doi.org/10.1007/s11746-015-2608-5
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DOI: https://doi.org/10.1007/s11746-015-2608-5